New valuable indigoid vat dyestuffs



Patented May 2, 1933 UNITED STATES PATENT oF icE- KARL THIESS ANDTHEODOR MEISSNERI, F FRANKFORT-ON-THE-MAIN, GERMANY, AS-

SIGNORS TO GENERAL ANILINE vWORKS, INQ, OF NEW YORK, N. Y., A CORPORA-TION OF DELAWARE NEW VALUABLE INDIGOID VAT DYESTUFFS No Drawing.Application filed March '31, 1932, Serial No. 602,405, and in GermanyApril 16, 1931.

The present invention relates to new valuable indigoid vat dyestuffs,more particularly it relates to compounds of the following generalformula:

wherein R stands for an alkyl group and the two Xs or the two Ysrepresent a further condensed benzene nucleus.

The new dyestufi's are distinguished by a great tinctorial power andgood fastness properties, especially by a comparatively very goodfastness to light. The dystuf'fs,

when applied to the fiber with a reducing agent, are rapidly fixed onbeing steamed and they, therefore, are valuable in cloth print- The newcompounds may be prepared in various manners. Thus, for instance, a 1.2-

or a 2.l-naphthisatin-alpha-compound may be condensed with6-alkoXy-3-hydr-oXythionaphthene or 1.2- or 2.1-naphthindoxyl'may becondensed with a 6-alkoxy-3-hydroXy-lthionaphthene-alpha-compound. Thecondensation may be performed in the of a solvent or a diluent.

The following examples serve to illustrate the invention, but they arenot intended to 375 limit it thereto, the parts being by weight:

(1) 20 parts of 2.1-naphthisatin are warmed with 24: parts of phosphoruspentachloride in 250 parts of chlorobenzene and A thus transformed into2.1-naphthisatin-al pha-chloride. To this suspension a warm solution of18 parts of 6-methoxy-3-hydroxyl-thionaphthene in chlorobenzene is addedat C. to C. The dyestuff at once precipitates in the form of crystals.By shortly warming on th steam-bath, the condensation presence greentints and is well suited for being used in 55 olo h-printing. It hasthe-following formula dbl \S ooHa (2) By using in Example 1 instead of6- methoXy-3-hydroxy l thionaphthene 19.4 parts of6-ethoxy-3-hydroxy-l-thi-onaphthene and proceeding in the mannerindicated in that example, there is obtained 6-ethoXy-2-thionaphthene-t.5-benz-2-indolindigo which has properties very similarto those of the dyestufi' obtainable according to Example'l;

Similar dyestufis may also be obtained, by using instead of themethoxyand ethoxy compounds other alkoXy compounds as, for instance, thepropyloxyor butyloxy compounds. i V

(3) 2O parts'of 12-naphthisatin are transformed into1.2-naphthisatin-alpha-chloride by warming with 2% parts ofphosphoruspentachloride in 250 parts of chlorobenzene. To the emulsionobtained there is introduced at8Q C. to 90 C. a warm solution of 18parts of 6-meth'0xy-3-hydroXy-1-thionaphthene in chlorobenzene.6-methoXy-2-thionaphthene- 6.7-benZ-2-indolindigo precipitates at'oncein the form of crystals. By shortly heating on the steam-bath,thecondensation is finished and the product is worked up as described inExample 1. The dy-estuff dyes the fiber from a yellow vat olive-greentints similar to those obtained with the dyestuff of Example 1. Itsother properties are identical with those of the dyestuff of Example 1and it corresponds with the following formula:

O J NH 00113 (4:) 18.3 parts of 2.1-naphthindoxyl (obtainable accordingto the process described in Berichte der deutschen, chemischenGresellscha'ft, vol. 31, page 1816) are heated in a reflux apparatuswith 31.2 parts of 6-methoxy-3-hydroxythionaphthene-2-para-dimethylaminoanil in 300 parts ofboiling chlorobenzene, while stirring, until an increase of theformation of the dyestuff can no longer be detected. After cooling, the6r-methoxy-2- thionaphthene-4.5-benz 2-indolindigo which has beenformed, is filtered by suction, washed first with chlorobenzene and thenwith alcohol and dried. It is identical with the dyestuif obtainableaccording to Example 1.

We claim:

1. As new products, the compounds of the following general formula: s

O V x o\ i g Y N 5 OR O i l n x I N/ 5 OR 7 Y H wherein R stands formethyl or ethyl and the two Xs or the two Ys represent a furthercondensed benzene nucleus, said dyestufls having a great tinctorialpower and good fastness properties, especially to light, and beingsuitable for use in cloth printing.

3. As a new product, the compound of the following formula:

dissolvingin concentrated sulfuric acid to a blue solution and in hotchlorobenzene or hot nltrobenzene to a red solution, dyeing the fiberfrom a yellow vat olive-green tints andbeing valuable for use incloth-printing.

4;. As a new product, the compound of the following formula:

nitrobenzene to a red solution, dyeing the fiber from a yellow vatolive-green tints and being'valuable for use in cloth-printing.

In testimony whereof. we affix our signatures.

KARL THIESS. THEODOR MEISSNER.

